Aroyl-amino-diphthaloyl-acridones and process of preparing the same



Patented Apr. 23, 1929. 1

UNITED STATES PATENT OFFICE.

WALTER IIEG AND ALBERT J OB, OF ELBERFELD, GERMANY, ASSIGNORS '10GRASSELLI DYEBTUFF CORPORATION, OF NEW YORK, N. Y., A CORPORATION OFDELAWARE AROYL-AHINO-DIPHTHAI4OYL-ACRIDONES AND PROCESS OF PREPARING THESAME.

No Drawing. Application flledlay 28, 1927, Serial No. 193,722, and inGermany Kay 27, 1926.

The present invention relates to aroyl-amino-diphthaloyl-acridones ofthe general formula:

and R represents an aroyl radicle.

Our new compounds can be produced by m aroylating the mono amidodiphthaloylacrldones which are obtainable by nitrating adiphthaloyl-acridone and reducing the nitro compound thus obtained, asdescribed in our co-pending applications Ser. No. 193,723 and No.193,721, filed on May 23, 1927.

Our new vat dyestuffs are in dry state JI'OWIllSll powders, soluble inconcentrated sulfuric acid with orange shades, soluble in boiling nitrobenzole with violet colors. The following examples will illustrate ourinvention:

Emample 1.1 part by weight of the mono amino 3.4.5.6-diphthaloylacridone obtainable according to the co-pending applications Se.-

5 rial No. 193,7 23 and No. 193,721, by nitrating 3.4.5.6-diphthaloylacridone and reducing with aqueous sodium hydrosulfite solutions, is

- boiled with 3040 parts by weight of nitro benzole and 0.7 parts byweight of benzoyl chlo ride until the formation of the violent benzoylcompound is complete. The benzoyl mono amino 3.4.5.6-diphthaloylacridone is isolated by filtration after cooling. It dyes cotton fromthe hydrosulfite vat violet grey shades of excellent fastnessproperties, especially to light. It has the probable formula:

pound of 1.2.5.6 -diphthaloyl tainable according to copending apphc10I1S Serial N 0. 193,723 and No. 193,- 721, bynitrating1.2.5.6-diphthaloyl acridone and reducing the mono nitro compound withalkaline hydrosulfite, is dissolved in 30-40 parts by weight of nitrobenzole and boiled. After the addition of 0.7 parts by weight of benzoylchloride, a crystalline benzoyl mono amino 1.2.5.6-diphthaloyl acridoneis obtained in bone shaped (prismatic) leaflets possessing a bronzelustre, soluble in concentrated sulfuric acid with an orange color, anddyeing cotton from a violet vat in strong olive grey shades of.excellent fastness properties. It dissolves in boiling nitro benzolewith violet shades. It has the probable formula:

g NH I t I NHCOZCIHE n Example 3.In the same manner as above the aminocompounds of Examples 1 and 2 can also be acylated with other aroylhalogenides for instance orthoor para-chlorobenzoyl chloride. From themono amino compound of 1.2.5.6-diphthaloyl acridone andortho-chlorobenzoyl chloride a vat dyestufi I a hydrosulfite vat ingreyish colors, dilficultly soluble in organic solutions such as nitrobenzole.

2; Ase new product the ben'zoylated mono; 3. Materials dyed with theproduct deamino 1.2.5.6-diphthaloyl acriclone which-is in scribedin'claim 1.- dry state a crystal powder of bone shaped 4. Materials dyedwith the product deleaflets, poseessing a bronzelustre, soluble inscribed in claim 2 v I 5 sulfuric acid with an orange color and dyeingIn testimony whereof, we aflix our signathe fibre from a violet vat instrong olive grey tures. 4 shades of'excellent fastness properties,solu- WALTER MIEG.

ble in boiling nitro benzole with violet shades. ALBERT JOB.

